Natural Product: NPC264546

Natural Product ID:  NPC264546
Common Name:   Negundoin C
IUPAC Name:   [(2S,4aS,5R,5'E,6R,8aS)-1,1,4a,6-tetramethyl-5'-(2-oxoethylidene)spiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxolane]-2-yl] acetate
Synonyms:   Negundoin C
Molecular Formula:   C21H32O4
Standard InCHIKey:  YUIOUOHLEHUTMC-CXDIRSQKSA-N
Standard InCHI:  InChI=1S/C21H32O4/c1-14-6-7-17-19(3,4)18(24-15(2)23)9-11-20(17,5)21(14)12-8-16(25-21)10-13-22/h10,13-14,17-18H,6-9,11-12H2,1-5H3/b16-10+/t14-,17+,18+,20+,21-/m1/s1
Canonical SMILES:  O=C/C=C/1CC[C@@]2(O1)[C@H](C)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)OC(=O)C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds PMID[19931461]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 0.4 % 20630628
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 2.06 % 20630628
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 120 nM 18426901

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC264546 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9176 High Similarity NPC106332
0.907 High Similarity NPC170633
0.8765 High Similarity NPC219809
0.8315 Intermediate Similarity NPC291665
0.8152 Intermediate Similarity NPC7349
0.8085 Intermediate Similarity NPC475380
0.8085 Intermediate Similarity NPC209297
0.8065 Intermediate Similarity NPC105490
0.8065 Intermediate Similarity NPC140277
0.8023 Intermediate Similarity NPC469802
0.8 Intermediate Similarity NPC311241
0.8 Intermediate Similarity NPC475446
0.7978 Intermediate Similarity NPC474013
0.7957 Intermediate Similarity NPC474185
0.7955 Intermediate Similarity NPC476927
0.7938 Intermediate Similarity NPC119467
0.7938 Intermediate Similarity NPC475767
0.7931 Intermediate Similarity NPC170303
0.7917 Intermediate Similarity NPC72647
0.7917 Intermediate Similarity NPC107806
0.7917 Intermediate Similarity NPC278673
0.7912 Intermediate Similarity NPC93411
0.7895 Intermediate Similarity NPC194132
0.7865 Intermediate Similarity NPC306951
0.7865 Intermediate Similarity NPC96055
0.7849 Intermediate Similarity NPC473675
0.7841 Intermediate Similarity NPC256112
0.7835 Intermediate Similarity NPC471413
0.7812 Intermediate Similarity NPC100912
0.7802 Intermediate Similarity NPC166857
0.7789 Intermediate Similarity NPC276110
0.7778 Intermediate Similarity NPC474575
0.7766 Intermediate Similarity NPC12297
0.7755 Intermediate Similarity NPC471412
0.7742 Intermediate Similarity NPC302280
0.7742 Intermediate Similarity NPC328141
0.7742 Intermediate Similarity NPC474842
0.7742 Intermediate Similarity NPC475965
0.7723 Intermediate Similarity NPC179380
0.7723 Intermediate Similarity NPC302788
0.7723 Intermediate Similarity NPC475074
0.7708 Intermediate Similarity NPC151725
0.7708 Intermediate Similarity NPC122324
0.7708 Intermediate Similarity NPC106425
0.7701 Intermediate Similarity NPC283789
0.7692 Intermediate Similarity NPC214315
0.7684 Intermediate Similarity NPC269729
0.7684 Intermediate Similarity NPC57117
0.7684 Intermediate Similarity NPC279410
0.7684 Intermediate Similarity NPC119562
0.7677 Intermediate Similarity NPC109195
0.7677 Intermediate Similarity NPC475038
0.7677 Intermediate Similarity NPC162973
0.7667 Intermediate Similarity NPC471367
0.7667 Intermediate Similarity NPC102048
0.7653 Intermediate Similarity NPC470906
0.7653 Intermediate Similarity NPC324841
0.764 Intermediate Similarity NPC286786
0.764 Intermediate Similarity NPC471218
0.764 Intermediate Similarity NPC2524
0.7634 Intermediate Similarity NPC50070
0.7634 Intermediate Similarity NPC82876
0.7629 Intermediate Similarity NPC51499
0.7624 Intermediate Similarity NPC471206
0.7614 Intermediate Similarity NPC269791
0.7609 Intermediate Similarity NPC175293
0.7604 Intermediate Similarity NPC274417
0.76 Intermediate Similarity NPC120009
0.76 Intermediate Similarity NPC120321
0.76 Intermediate Similarity NPC282233
0.76 Intermediate Similarity NPC254202
0.76 Intermediate Similarity NPC95585
0.7579 Intermediate Similarity NPC473678
0.7579 Intermediate Similarity NPC38232
0.7576 Intermediate Similarity NPC268829
0.7576 Intermediate Similarity NPC247701
0.7576 Intermediate Similarity NPC25177
0.7576 Intermediate Similarity NPC222875
0.7576 Intermediate Similarity NPC11974
0.7576 Intermediate Similarity NPC295110
0.7556 Intermediate Similarity NPC139206
0.7556 Intermediate Similarity NPC132386
0.7556 Intermediate Similarity NPC473742
0.7553 Intermediate Similarity NPC78973
0.7551 Intermediate Similarity NPC275086
0.7551 Intermediate Similarity NPC325229
0.7551 Intermediate Similarity NPC218107
0.7528 Intermediate Similarity NPC195334
0.7528 Intermediate Similarity NPC290495
0.7527 Intermediate Similarity NPC470612
0.7527 Intermediate Similarity NPC470613
0.7527 Intermediate Similarity NPC80335
0.7526 Intermediate Similarity NPC8954
0.7526 Intermediate Similarity NPC16967
0.7526 Intermediate Similarity NPC29952
0.7526 Intermediate Similarity NPC471039
0.7526 Intermediate Similarity NPC94905
0.7525 Intermediate Similarity NPC165969
0.75 Intermediate Similarity NPC161998
0.75 Intermediate Similarity NPC22388
0.75 Intermediate Similarity NPC474970
0.75 Intermediate Similarity NPC128488
0.75 Intermediate Similarity NPC44083
0.75 Intermediate Similarity NPC175145
0.75 Intermediate Similarity NPC153987
0.75 Intermediate Similarity NPC471219
0.75 Intermediate Similarity NPC475069
0.75 Intermediate Similarity NPC304968
0.75 Intermediate Similarity NPC131813
0.75 Intermediate Similarity NPC103491
0.75 Intermediate Similarity NPC471040
0.75 Intermediate Similarity NPC471369
0.7475 Intermediate Similarity NPC35751
0.7475 Intermediate Similarity NPC38855
0.7475 Intermediate Similarity NPC251680
0.7475 Intermediate Similarity NPC471041
0.7474 Intermediate Similarity NPC329842
0.7474 Intermediate Similarity NPC473944
0.7474 Intermediate Similarity NPC72845
0.7473 Intermediate Similarity NPC32223
0.7473 Intermediate Similarity NPC299963
0.7471 Intermediate Similarity NPC470428
0.7451 Intermediate Similarity NPC34768
0.7451 Intermediate Similarity NPC218158
0.7449 Intermediate Similarity NPC198549
0.7449 Intermediate Similarity NPC113976
0.7449 Intermediate Similarity NPC99726
0.7447 Intermediate Similarity NPC471043
0.7447 Intermediate Similarity NPC246028
0.7447 Intermediate Similarity NPC314727
0.7444 Intermediate Similarity NPC472504
0.7426 Intermediate Similarity NPC478057
0.7426 Intermediate Similarity NPC160583
0.7426 Intermediate Similarity NPC45897
0.7426 Intermediate Similarity NPC176883
0.7426 Intermediate Similarity NPC10232
0.7426 Intermediate Similarity NPC196471
0.7426 Intermediate Similarity NPC189588
0.7426 Intermediate Similarity NPC187302
0.7426 Intermediate Similarity NPC97487
0.7423 Intermediate Similarity NPC472189
0.7423 Intermediate Similarity NPC279974
0.7423 Intermediate Similarity NPC471362
0.7423 Intermediate Similarity NPC281134
0.7423 Intermediate Similarity NPC471372
0.7419 Intermediate Similarity NPC478104
0.7416 Intermediate Similarity NPC281880
0.74 Intermediate Similarity NPC472554
0.74 Intermediate Similarity NPC168319
0.74 Intermediate Similarity NPC194028
0.7396 Intermediate Similarity NPC475657
0.7396 Intermediate Similarity NPC79117
0.7391 Intermediate Similarity NPC164424
0.7391 Intermediate Similarity NPC2709
0.7391 Intermediate Similarity NPC476602
0.7386 Intermediate Similarity NPC476949
0.7379 Intermediate Similarity NPC319438
0.7374 Intermediate Similarity NPC119036
0.7374 Intermediate Similarity NPC252295
0.7368 Intermediate Similarity NPC475776
0.7363 Intermediate Similarity NPC79945
0.7353 Intermediate Similarity NPC470297
0.7347 Intermediate Similarity NPC111684
0.7347 Intermediate Similarity NPC234993
0.7347 Intermediate Similarity NPC307164
0.7347 Intermediate Similarity NPC276103
0.7347 Intermediate Similarity NPC471903
0.7347 Intermediate Similarity NPC253115
0.7347 Intermediate Similarity NPC475178
0.7347 Intermediate Similarity NPC304899
0.7347 Intermediate Similarity NPC54248
0.7347 Intermediate Similarity NPC58052
0.7347 Intermediate Similarity NPC171598
0.7347 Intermediate Similarity NPC134072
0.734 Intermediate Similarity NPC224145
0.734 Intermediate Similarity NPC473879
0.734 Intermediate Similarity NPC263079
0.734 Intermediate Similarity NPC473229
0.7333 Intermediate Similarity NPC474567
0.7333 Intermediate Similarity NPC108476
0.7333 Intermediate Similarity NPC475665
0.7333 Intermediate Similarity NPC159148
0.7333 Intermediate Similarity NPC25554
0.7333 Intermediate Similarity NPC142163
0.7333 Intermediate Similarity NPC476101
0.7327 Intermediate Similarity NPC472815
0.7327 Intermediate Similarity NPC476081
0.7327 Intermediate Similarity NPC472552
0.7327 Intermediate Similarity NPC11956
0.732 Intermediate Similarity NPC477722
0.732 Intermediate Similarity NPC473435
0.732 Intermediate Similarity NPC471078
0.732 Intermediate Similarity NPC473431
0.732 Intermediate Similarity NPC473280
0.732 Intermediate Similarity NPC201725
0.732 Intermediate Similarity NPC191521
0.732 Intermediate Similarity NPC474922
0.7312 Intermediate Similarity NPC286153
0.7312 Intermediate Similarity NPC73038
0.7312 Intermediate Similarity NPC102996

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC264546 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7551 Intermediate Similarity NPD7638 Approved
0.7475 Intermediate Similarity NPD7639 Approved
0.7475 Intermediate Similarity NPD7640 Approved
0.7282 Intermediate Similarity NPD6008 Approved
0.7143 Intermediate Similarity NPD7748 Approved
0.7143 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7900 Approved
0.7128 Intermediate Similarity NPD7521 Approved
0.7128 Intermediate Similarity NPD7334 Approved
0.7128 Intermediate Similarity NPD6684 Approved
0.7128 Intermediate Similarity NPD7146 Approved
0.7128 Intermediate Similarity NPD6409 Approved
0.7128 Intermediate Similarity NPD5330 Approved
0.7071 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD3573 Approved
0.703 Intermediate Similarity NPD4225 Approved
0.6979 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6979 Remote Similarity NPD6672 Approved
0.6979 Remote Similarity NPD5737 Approved
0.6979 Remote Similarity NPD6903 Approved
0.6939 Remote Similarity NPD7515 Phase 2
0.6931 Remote Similarity NPD7902 Approved
0.6907 Remote Similarity NPD6051 Approved
0.6848 Remote Similarity NPD7525 Registered
0.6842 Remote Similarity NPD1694 Approved
0.6827 Remote Similarity NPD7632 Discontinued
0.6822 Remote Similarity NPD6899 Approved
0.6822 Remote Similarity NPD6881 Approved
0.6792 Remote Similarity NPD5739 Approved
0.6792 Remote Similarity NPD6675 Approved
0.6792 Remote Similarity NPD7128 Approved
0.6792 Remote Similarity NPD6402 Approved
0.6735 Remote Similarity NPD6673 Approved
0.6735 Remote Similarity NPD6080 Approved
0.6735 Remote Similarity NPD6904 Approved
0.6729 Remote Similarity NPD5697 Approved
0.67 Remote Similarity NPD6399 Phase 3
0.6697 Remote Similarity NPD6883 Approved
0.6697 Remote Similarity NPD7290 Approved
0.6697 Remote Similarity NPD7102 Approved
0.6696 Remote Similarity NPD7503 Approved
0.6667 Remote Similarity NPD6011 Approved
0.6667 Remote Similarity NPD7320 Approved
0.6667 Remote Similarity NPD4632 Approved
0.6636 Remote Similarity NPD6617 Approved
0.6636 Remote Similarity NPD8130 Phase 1
0.6636 Remote Similarity NPD6869 Approved
0.6636 Remote Similarity NPD6649 Approved
0.6636 Remote Similarity NPD6650 Approved
0.6636 Remote Similarity NPD6847 Approved
0.6635 Remote Similarity NPD6648 Approved
0.6634 Remote Similarity NPD6001 Approved
0.6606 Remote Similarity NPD6014 Approved
0.6606 Remote Similarity NPD6012 Approved
0.6606 Remote Similarity NPD6372 Approved
0.6606 Remote Similarity NPD6013 Approved
0.6606 Remote Similarity NPD6373 Approved
0.6602 Remote Similarity NPD6084 Phase 2
0.6602 Remote Similarity NPD6083 Phase 2
0.66 Remote Similarity NPD6079 Approved
0.6598 Remote Similarity NPD3618 Phase 1
0.6579 Remote Similarity NPD7328 Approved
0.6579 Remote Similarity NPD7327 Approved
0.6577 Remote Similarity NPD8297 Approved
0.6577 Remote Similarity NPD6882 Approved
0.6574 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6574 Remote Similarity NPD5701 Approved
0.6571 Remote Similarity NPD5344 Discontinued
0.6566 Remote Similarity NPD5328 Approved
0.6559 Remote Similarity NPD7645 Phase 2
0.6525 Remote Similarity NPD7492 Approved
0.6522 Remote Similarity NPD7516 Approved
0.6514 Remote Similarity NPD6686 Approved
0.6505 Remote Similarity NPD4697 Phase 3
0.6491 Remote Similarity NPD6009 Approved
0.6486 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7507 Approved
0.6471 Remote Similarity NPD6616 Approved
0.6466 Remote Similarity NPD6319 Approved
0.6466 Remote Similarity NPD8377 Approved
0.6466 Remote Similarity NPD6054 Approved
0.6466 Remote Similarity NPD8294 Approved
0.6465 Remote Similarity NPD5208 Approved
0.6458 Remote Similarity NPD6695 Phase 3
0.6455 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6441 Remote Similarity NPD7604 Phase 2
0.6436 Remote Similarity NPD8035 Phase 2
0.6436 Remote Similarity NPD5693 Phase 1
0.6436 Remote Similarity NPD8034 Phase 2
0.6436 Remote Similarity NPD6050 Approved
0.6429 Remote Similarity NPD6098 Approved
0.6417 Remote Similarity NPD7078 Approved
0.641 Remote Similarity NPD8296 Approved
0.641 Remote Similarity NPD8380 Approved
0.641 Remote Similarity NPD8033 Approved
0.641 Remote Similarity NPD8335 Approved
0.641 Remote Similarity NPD8379 Approved
0.641 Remote Similarity NPD8378 Approved
0.641 Remote Similarity NPD5983 Phase 2
0.6408 Remote Similarity NPD5695 Phase 3
0.6396 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6392 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6383 Remote Similarity NPD4195 Approved
0.6381 Remote Similarity NPD5696 Approved
0.6373 Remote Similarity NPD4202 Approved
0.6364 Remote Similarity NPD7736 Approved
0.6356 Remote Similarity NPD6370 Approved
0.6348 Remote Similarity NPD7115 Discovery
0.6346 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6346 Remote Similarity NPD5222 Approved
0.6346 Remote Similarity NPD5221 Approved
0.6337 Remote Similarity NPD5207 Approved
0.6337 Remote Similarity NPD5692 Phase 3
0.6333 Remote Similarity NPD6336 Discontinued
0.6327 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6325 Remote Similarity NPD6059 Approved
0.6321 Remote Similarity NPD5285 Approved
0.6321 Remote Similarity NPD4696 Approved
0.6321 Remote Similarity NPD5286 Approved
0.6311 Remote Similarity NPD7319 Approved
0.6311 Remote Similarity NPD5282 Discontinued
0.6304 Remote Similarity NPD7339 Approved
0.6304 Remote Similarity NPD6942 Approved
0.6293 Remote Similarity NPD6335 Approved
0.6286 Remote Similarity NPD5173 Approved
0.6286 Remote Similarity NPD4755 Approved
0.6281 Remote Similarity NPD8293 Discontinued
0.6275 Remote Similarity NPD7637 Suspended
0.6275 Remote Similarity NPD5694 Approved
0.6273 Remote Similarity NPD6412 Phase 2
0.6271 Remote Similarity NPD6016 Approved
0.6271 Remote Similarity NPD6015 Approved
0.6263 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6262 Remote Similarity NPD5223 Approved
0.6261 Remote Similarity NPD6274 Approved
0.6261 Remote Similarity NPD6868 Approved
0.6239 Remote Similarity NPD7101 Approved
0.6239 Remote Similarity NPD7100 Approved
0.6237 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6224 Remote Similarity NPD3666 Approved
0.6224 Remote Similarity NPD3665 Phase 1
0.6224 Remote Similarity NPD4786 Approved
0.6224 Remote Similarity NPD3133 Approved
0.6224 Remote Similarity NPD3668 Phase 3
0.6218 Remote Similarity NPD5988 Approved
0.6207 Remote Similarity NPD6317 Approved
0.6204 Remote Similarity NPD4633 Approved
0.6204 Remote Similarity NPD5211 Phase 2
0.6204 Remote Similarity NPD5226 Approved
0.6204 Remote Similarity NPD5225 Approved
0.6204 Remote Similarity NPD5224 Approved
0.62 Remote Similarity NPD7750 Discontinued
0.62 Remote Similarity NPD7524 Approved
0.6196 Remote Similarity NPD6924 Approved
0.6196 Remote Similarity NPD6926 Approved
0.6186 Remote Similarity NPD3667 Approved
0.6168 Remote Similarity NPD4700 Approved
0.6154 Remote Similarity NPD6313 Approved
0.6154 Remote Similarity NPD6314 Approved
0.6147 Remote Similarity NPD5175 Approved
0.6147 Remote Similarity NPD5174 Approved
0.6147 Remote Similarity NPD6052 Approved
0.6146 Remote Similarity NPD4695 Discontinued
0.6146 Remote Similarity NPD6930 Phase 2
0.6146 Remote Similarity NPD6931 Approved
0.614 Remote Similarity NPD6053 Discontinued
0.6134 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6106 Remote Similarity NPD4634 Approved
0.6105 Remote Similarity NPD6114 Approved
0.6105 Remote Similarity NPD6697 Approved
0.6105 Remote Similarity NPD6118 Approved
0.6105 Remote Similarity NPD6115 Approved
0.6091 Remote Similarity NPD5141 Approved
0.6078 Remote Similarity NPD4753 Phase 2
0.6078 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6075 Remote Similarity NPD5290 Discontinued
0.6071 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6064 Remote Similarity NPD6933 Approved
0.6042 Remote Similarity NPD6929 Approved
0.604 Remote Similarity NPD4251 Approved
0.604 Remote Similarity NPD4751 Clinical (unspecified phase)
0.604 Remote Similarity NPD4250 Approved
0.6038 Remote Similarity NPD7732 Phase 3
0.6038 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6033 Remote Similarity NPD6067 Discontinued
0.6033 Remote Similarity NPD8328 Phase 3
0.6023 Remote Similarity NPD2685 Clinical (unspecified phase)
0.602 Remote Similarity NPD4223 Phase 3
0.602 Remote Similarity NPD4221 Approved
0.6018 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6 Remote Similarity NPD6908 Approved
0.6 Remote Similarity NPD6909 Approved
0.6 Remote Similarity NPD4754 Approved
0.6 Remote Similarity NPD6932 Approved
0.6 Remote Similarity NPD5329 Approved
0.5982 Remote Similarity NPD6614 Approved
0.5979 Remote Similarity NPD7509 Discontinued
0.5978 Remote Similarity NPD4243 Approved
0.5968 Remote Similarity NPD6033 Approved

Structure

External Identifiers

PubChem CID   46229719
ChEMBL   CHEMBL591822
ZINC  

Physicochemical Properties

Molecular Weight:  348.23
ALogP:  1.137
MLogP:  3.33
XLogP:  4.377
# Rotatable Bonds:  8
Polar Surface Area:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  25

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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